CA2334568C - Derives de 3-(2-oxo-[1,3']bipyrrolidinyl-3-ylidenemethyl)-cephemes - Google Patents

Derives de 3-(2-oxo-[1,3']bipyrrolidinyl-3-ylidenemethyl)-cephemes Download PDF

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Publication number
CA2334568C
CA2334568C CA002334568A CA2334568A CA2334568C CA 2334568 C CA2334568 C CA 2334568C CA 002334568 A CA002334568 A CA 002334568A CA 2334568 A CA2334568 A CA 2334568A CA 2334568 C CA2334568 C CA 2334568C
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CA
Canada
Prior art keywords
hydrogen
oxo
ocor
compound according
infectious disease
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Expired - Lifetime
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CA002334568A
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English (en)
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CA2334568A1 (fr
Inventor
Paul Hebeisen
Christian Hubschwerlen
Jean-Luc Specklin
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Basilea Pharmaceutica AG
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Basilea Pharmaceutica AG
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Publication of CA2334568A1 publication Critical patent/CA2334568A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/48—Methylene radicals, substituted by hetero rings
    • C07D501/56—Methylene radicals, substituted by hetero rings with the 7-amino radical acylated by carboxylic acids containing hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cephalosporin Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention concerne des composés représentés par la formule générale (I). Dans cette formule, R<1> est hydrogène, C1-6-alkyle, éventuellement substitué par un fluoro, ou C3-6-cycloalkyle. R<2> est hydrogène ou un groupe appartenant aux -CH2C(=CHR)-COOR, -CH2OCOR, -CH(R)OCOR, -CH(R)OCOOR, -CH(OCOR)OCOR et -CH2OCOR et (II). R<3> est hydrogène ou un groupe appartenant aux -CH2C(=CH2)-COOR, -COOCH2C(=CHR)-COOR, -COOCH2OCOR, -COOCH(R)OCOR, -COOCH(R)OCOOR, -COOCH(OCOR)OCOR et -COOCH2COCH2OCOR et (III). En outre dans la mesure où l'un de R<2> et R<3> est hydrogène et que l'autre de R<2> et R<3> n'est pas hydrogène, R est hydrogène ou C1-6-alkyle. R<4> est hydrogène ou hydroxy. R<5> est hydrogène ou omega -hydroxyalkyle. Enfin, X est CH ou N. L'invention concerne également des sels pharmaceutiquement acceptables de ces composés, ainsi que des hydrates de ces composés et de leurs sels. L'invention concerne enfin l'utilisation des composés représentés par la formule générale (I) et des sels pharmaceutiquement acceptables de ces composés ainsi que l'utilisation des hydrates de ces composés et de leurs sels pour la fabrication de préparations pharmaceutiques renfermant de tels composés.
CA002334568A 1998-06-15 1999-06-07 Derives de 3-(2-oxo-[1,3']bipyrrolidinyl-3-ylidenemethyl)-cephemes Expired - Lifetime CA2334568C (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP98110888.9 1998-06-15
EP98110888 1998-06-15
EP98117099.6 1998-09-10
EP98117099 1998-09-10
PCT/EP1999/003907 WO1999065920A1 (fr) 1998-06-15 1999-06-07 Derives de 3-(2-oxo-[1,3']bipyrrolidinyl-3-ylidenemethyl)-cephemes

Publications (2)

Publication Number Publication Date
CA2334568A1 CA2334568A1 (fr) 1999-12-23
CA2334568C true CA2334568C (fr) 2009-02-24

Family

ID=26149347

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002334568A Expired - Lifetime CA2334568C (fr) 1998-06-15 1999-06-07 Derives de 3-(2-oxo-[1,3']bipyrrolidinyl-3-ylidenemethyl)-cephemes

Country Status (28)

Country Link
EP (1) EP1087980B1 (fr)
JP (1) JP3872955B2 (fr)
KR (1) KR100411915B1 (fr)
CN (1) CN1136222C (fr)
AR (1) AR018675A1 (fr)
AT (1) ATE231871T1 (fr)
AU (1) AU754732B2 (fr)
BE (1) BE2014C034I2 (fr)
BR (2) BRPI9911178C1 (fr)
CA (1) CA2334568C (fr)
CO (1) CO5080758A1 (fr)
DE (1) DE69905162T2 (fr)
DK (1) DK1087980T3 (fr)
ES (1) ES2190222T3 (fr)
FR (1) FR14C0044I2 (fr)
GT (1) GT199900084A (fr)
HU (1) HUP0105426A3 (fr)
ID (1) ID27686A (fr)
IL (1) IL139872A0 (fr)
LU (1) LU92564I2 (fr)
MA (1) MA26650A1 (fr)
NO (1) NO20006350L (fr)
PA (1) PA8475701A1 (fr)
PE (1) PE20000645A1 (fr)
PL (1) PL344994A1 (fr)
SV (1) SV1999000075A (fr)
TN (1) TNSN99114A1 (fr)
WO (1) WO1999065920A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU6267100A (en) * 1999-07-07 2001-01-30 F. Hoffmann-La Roche Ag Vinylpyrrolidinone derivatives with substituted thiazole ring
ES2272372T3 (es) 2000-04-19 2007-05-01 Basilea Pharmaceutica Ag Procedimiento para la preparacion de derivados de asparagina.
US6504025B2 (en) 2000-05-24 2003-01-07 Basilea Pharmaceutica Ag Process for the preparation of vinyl-pyrrolidinone cephalosporin derivatives
BRPI0408716B1 (pt) * 2003-03-27 2017-08-29 Basilea Pharmaceutica Ag. Cefalosporin in crystalline form, process for its preparation and its uses, and preparation of cephalosporin
EP1656930A1 (fr) * 2004-11-10 2006-05-17 Basilea Pharmaceutica AG Formulation lyophilisée stabilisée pour des dérivés des céphalosporines
AR071318A1 (es) 2008-04-15 2010-06-09 Basilea Pharmaceutica Ag Benzhidril ester del acido (6r,7r)-7-{2-(5-amino-[1,2,4]tiadiazol-3-il)-2-[(z)-tritiloxiimino]-acetilamino}-3-[(r)-1'-terc-butoxicarbonil-2-oxo-[1,3']bipirrolidinil-(3e)-ilidenometil]-8-oxo-5-tia-1-aza-biciclo[4.2.0]oct-2-eno-2-carboxilico cristalino; su elaboracion y uso
WO2010072672A1 (fr) 2008-12-24 2010-07-01 Basilea Pharmaceutica Ag Nouveaux polymorphes cristallins du ceftobiprole
EP2435442B1 (fr) * 2009-05-25 2016-01-13 Sandoz AG Procédé de fabrication de ceftobiprol medocaril
BR112012028678A2 (pt) 2010-05-10 2015-09-15 Basilea Pharmaceutica Internat Ltd processo de oxidação para preparar derivados de 3-formil-cefem

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0841339B1 (fr) * 1996-11-06 2007-02-21 Basilea Pharmaceutica AG Dérivés de vinylpyrrolidone-céphalosporine
TW415949B (en) * 1996-12-19 2000-12-21 Hoffmann La Roche Vinyl pyrrolidine cephalosporin derivatives with basic substituents

Also Published As

Publication number Publication date
TNSN99114A1 (fr) 2005-11-10
JP2002518401A (ja) 2002-06-25
CN1136222C (zh) 2004-01-28
FR14C0044I1 (fr) 2014-07-18
AU754732B2 (en) 2002-11-21
CO5080758A1 (es) 2001-09-25
MA26650A1 (fr) 2004-12-20
BR9911178A (pt) 2001-03-13
DE69905162D1 (de) 2003-03-06
DK1087980T3 (da) 2003-05-26
CA2334568A1 (fr) 1999-12-23
FR14C0044I2 (fr) 2015-02-20
LU92564I2 (fr) 2014-12-01
BRPI9911178C1 (pt) 2021-05-25
DE69905162T2 (de) 2003-12-24
HUP0105426A3 (en) 2002-12-28
AR018675A1 (es) 2001-11-28
JP3872955B2 (ja) 2007-01-24
BR9911178B1 (pt) 2013-10-29
HUP0105426A2 (hu) 2002-05-29
NO20006350D0 (no) 2000-12-13
EP1087980B1 (fr) 2003-01-29
CN1305484A (zh) 2001-07-25
BE2014C034I2 (en) 2018-08-24
SV1999000075A (es) 2000-05-02
ATE231871T1 (de) 2003-02-15
KR20010052866A (ko) 2001-06-25
GT199900084A (es) 2000-12-05
PE20000645A1 (es) 2000-07-26
EP1087980A1 (fr) 2001-04-04
IL139872A0 (en) 2002-02-10
ES2190222T3 (es) 2003-07-16
AU4508199A (en) 2000-01-05
PA8475701A1 (es) 2000-09-29
ID27686A (id) 2001-04-19
PL344994A1 (en) 2001-11-19
NO20006350L (no) 2000-12-13
WO1999065920A1 (fr) 1999-12-23
BRPI9911178B8 (pt) 2017-03-07
KR100411915B1 (ko) 2003-12-18

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